HRP20191114T1 - Glycogen-based cationic polymers - Google Patents

Glycogen-based cationic polymers Download PDF

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HRP20191114T1
HRP20191114T1 HRP20191114TT HRP20191114T HRP20191114T1 HR P20191114 T1 HRP20191114 T1 HR P20191114T1 HR P20191114T T HRP20191114T T HR P20191114TT HR P20191114 T HRP20191114 T HR P20191114T HR P20191114 T1 HRP20191114 T1 HR P20191114T1
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Vincenzo Russo
Elisa Liberati
Nicola Cazzolla
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Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A.
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    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/18—Reserve carbohydrates, e.g. glycogen, inulin, laminarin; Derivatives thereof

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Claims (15)

1. Kationski polimer na bazi glikogena, naznačen time, da obuhvaća najmanje jednu ponavljajuću jedinicu odabranu iz skupine koja se sastoji od sljedećih: (a) u kojoj su skupine R koje mogu biti iste ili različite, atom vodika, karboksimetil-skupina, opcionalno u obliku soli s farmaceutski prihvatljivom organskom ili anorganskom bazom, ili skupina koja sadrži dušik odabrana od sljedećih: NH2-(C1-C6)alkil, [N,N-di(C1-C6)alkilamino]-(C1-C6)alkil, NH2-{[(C1-C6)alkil-di(C1-C6)alkilamonij]}-(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkil-di(C1-C6)alkilamonij}-(C1-C6)alkil, NH2-[(C1-C6)alkilamino]-(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkilamino}-(C1-C6)alkil, [tri(C1-C6)alkilamonij]-(C1-C6)alkil, azociklil-(C1-C6)alkil, gdje su (C1-C6)alkil-lanci koji mogu biti isti ili različiti, opcionalno supstituirani s jednom ili više hidroksil-skupina, i n je cijeli broj veći od ili jednak 1; i (b) u kojoj R1 je odabran od atoma vodika, karboksimetil-skupine, opcionalno u obliku soli s farmaceutski prihvatljivom organskom ili anorganskom bazom, ili od skupine koja sadrži dušik odabrane od sljedećih: NH2-(C1-C6)alkil, [N,N-di(C1-C6)alkilamino]-(C1-C6)alkil, NH2-[(C1-C6)alkil-di(C1-C6)alkilamonij] -(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkil-di(C1-C6)alkilamonij}-(C1-C6)alkil, NH2-[(C1-C6)alkilamino]-(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkilamino}-(C1-C6)alkil, [tri(C1-C6)alkilamonij]-(C1-C6)alkil, gdje su (C1-C6)alkil-lanci koji mogu biti isti ili različiti, opcionalno supstituirani s jednom ili više hidroksil-skupina; kod X1 i X2 koji mogu biti isti ili različiti, radi se o skupini –OH ili skupini koja sadrži dušik –NHR2, u kojoj je R2 odabran od sljedećih: atom vodika, (C1-C6)alkil, H-[NH-(C1-C6)alkil]p-, dok p je cijeli broj veći od ili jednak 1, a (C1-C6)alkil-skupine mogu biti iste ili različite; i m je cijeli broj veći od ili jednak 1; uz uvjet da je najmanje jedan između R, R1, X1 i X2, takva skupina koja sadrži dušik kao što je definirano, odgovarajuće za svaki od R, R1, X1 i X2, i uz uvjet da je navedeni kationski polimer na bazi glikogena različit od produkta koji se dobije reakcijom glikogena s N-(3-kloro-2-hidroksipropil)-trimetil-amonij-kloridom.1. A cationic polymer based on glycogen, characterized in that it comprises at least one repeating unit selected from the group consisting of the following: (And) where are R groups which may be the same or different, a hydrogen atom, a carboxymethyl group, optionally in the form of a salt with a pharmaceutically acceptable organic or inorganic base, or a nitrogen-containing group selected from the following: NH2-(C1-C6)alkyl, [N, N-di(C1-C6)alkylamino]-(C1-C6)alkyl, NH2-{[(C1-C6)alkyl-di(C1-C6)alkylammonium]}-(C1-C6)alkyl, {[N, N-di(C1-C6)alkylamino]-(C1-C6)alkyl-di(C1-C6)alkylammonium}-(C1-C6)alkyl, NH2-[(C1-C6)alkylamino]-(C1-C6) alkyl, {[N,N-di(C1-C6)alkylamino]-(C1-C6)alkylamino}(C1-C6)alkyl, [tri(C1-C6)alkylammonium]-(C1-C6)alkyl, azocyclyl -(C1-C6)alkyl, where the (C1-C6)alkyl chains, which may be the same or different, are optionally substituted with one or more hydroxyl groups, and n is an integer greater than or equal to 1; and (b) where R1 is selected from a hydrogen atom, a carboxymethyl group, optionally in the form of a salt with a pharmaceutically acceptable organic or inorganic base, or from a nitrogen-containing group selected from the following: NH2-(C1-C6)alkyl, [N,N-di(C1 -C6)alkylamino]-(C1-C6)alkyl, NH2-[(C1-C6)alkyl-di(C1-C6)alkylammonium] -(C1-C6)alkyl, {[N,N-di(C1-C6 )alkylamino]-(C1-C6)alkyl-di(C1-C6)alkylammonium}-(C1-C6)alkyl, NH2-[(C1-C6)alkylamino]-(C1-C6)alkyl, {[N,N-di(C1-C6)alkylamino]-(C1-C6)alkylamino}-(C1-C6)alkyl, [tri(C1-C6)alkylammonium]-(C1-C6)alkyl, where ( C1-C6) alkyl chains which may be the same or different, optionally substituted with one or more hydroxyl groups; in X1 and X2 which can be the same or different, it is an –OH group or a nitrogen-containing group –NHR2, wherein R2 is selected from the following: a hydrogen atom, (C1-C6)alkyl, H-[NH-(C1-C6)alkyl]p-, while p is an integer greater than or equal to 1, and (C1 -C6)alkyl groups can be the same or different; and m is an integer greater than or equal to 1; provided that at least one of R, R1, X1 and X2 is such a nitrogen-containing group as defined corresponding to each of R, R1, X1 and X2, and with the proviso that the specified cationic polymer based on glycogen is different from the product obtained by the reaction of glycogen with N-(3-chloro-2-hydroxypropyl)-trimethyl-ammonium-chloride. 2. Kationski polimer na bazi glikogena prema zahtjevu 1, naznačen time, da su navedene skupine R koje mogu biti iste ili različite, atom vodika, karboksimetil-skupina, opcionalno u obliku soli s farmaceutski prihvatljivom organskom ili anorganskom bazom, ili skupina koja sadrži dušik odabrana od sljedećih: [N,N-di(C1-C3)alkilamino]-(C1-C3)alkil, {[N,N-di(C1-C3)alkilamino]-(C1-C3)alkil-di(C1-C3)alkilamonij}-(C1-C3)alkil, {[N,N-di(C1-C3)alkilamino]-(C1-C3)alkilamino}-(C1-C3)alkil, [tri(C1-C3)alkilamonij]-(C1-C3)alkil, azociklil-(C1-C3)alkil, gdje su (C1-C3)alkil-lanci koji mogu biti isti ili različiti, opcionalno supstituirani s hidroksil-skupinom.2. Glycogen-based cationic polymer according to claim 1, characterized in that the R groups, which can be the same or different, are a hydrogen atom, a carboxymethyl group, optionally in the form of a salt with a pharmaceutically acceptable organic or inorganic base, or a nitrogen-containing group selected from the following: [N,N-di(C1-C3)alkylamino]-(C1-C3)alkyl, {[N,N-di(C1-C3)alkylamino]-(C1-C3)alkyl-di(C1-C3)alkylammonium}(C1-C3)alkyl, {[N,N-di(C1-C3)alkylamino]-(C1-C3)alkylamino}(C1-C3)alkyl, [tri(C1-C3)alkylammonium]-(C1-C3)alkyl, azocyclyl-(C1-C3)alkyl, where the (C1-C3)alkyl chains, which may be the same or different, are optionally substituted with a hydroxyl group. 3. Kationski polimer na bazi glikogena prema zahtjevu 2, naznačen time, da su navedene skupine R koje mogu biti iste ili različite, atom vodika, karboksimetil-skupina, opcionalno u obliku soli s farmaceutski prihvatljivom organskom ili anorganskom bazom, ili skupina koja sadrži dušik odabrana od sljedećih: N,N-dimetilamino-etil, N,N-dimetilamino-propil, N,N-dietilamino-etil, [(N,N-dimetilaminoetil)dimetilamonij]-etil, [(N,N-dimetilamino-propil)-dimetilamonij]-propil, [(N,N-dietilaminoetil)dietil-amonij]-etil, [trimetilamonij]-2-hidroksipropil, piperidil-N-etil ili morfolinil-N-etil.3. Glycogen-based cationic polymer according to claim 2, indicated by the fact that the R groups, which can be the same or different, are a hydrogen atom, a carboxymethyl group, optionally in the form of a salt with a pharmaceutically acceptable organic or inorganic base, or a nitrogen-containing group selected from the following: N,N-dimethylamino-ethyl, N,N-dimethylamino-propyl, N,N-diethylamino-ethyl, [(N,N-dimethylaminoethyl)dimethylammonium]-ethyl, [(N,N-dimethylamino-propyl )-dimethylammonium]-propyl, [(N,N-diethylaminoethyl)diethylammonium]-ethyl, [trimethylammonium]-2-hydroxypropyl, piperidyl-N-ethyl or morpholinyl-N-ethyl. 4. Kationski polimer na bazi glikogena prema bilo kojem od prethodnih zahtjeva, naznačen time, da R1 je atom vodika, karboksimetil-skupina, opcionalno u obliku soli s farmaceutski prihvatljivom organskom ili anorganskom bazom, ili skupina koja sadrži dušik odabrana od sljedećih: [N,N-di(C1-C3)alkilamino]-(C1-C3)alkil, {[N,N-di(C1-C3)alkilamino]-(C1-C3)alkil-di(C1-C3)alkilamonij}-(C1-C3)alkil, {[N,N-di(C1-C3)alkil-amino]-(C1-C3)alkilamino}-(C1-C3)alkil ili [tri(C1-C3)alkilamonij]-(C1-C3)alkil, gdje su (C1-C3)alkil-lanci koji mogu biti isti ili različiti, opcionalno supstituirani s hidroksil-skupinom.4. Glycogen-based cationic polymer according to any of the preceding claims, characterized in that R1 is a hydrogen atom, a carboxymethyl group, optionally in the form of a salt with a pharmaceutically acceptable organic or inorganic base, or a nitrogen-containing group selected from the following: [N ,N-di(C1-C3)alkylamino]-(C1-C3)alkyl, {[N,N-di(C1-C3)alkylamino]-(C1-C3)alkyl-di(C1-C3)alkylammonium}- (C1-C3)alkyl, {[N,N-di(C1-C3)alkyl-amino]-(C1-C3)alkylamino}(C1-C3)alkyl or [tri(C1-C3)alkylammonium]-( C1-C3)alkyl, where the (C1-C3)alkyl chains, which may be the same or different, are optionally substituted with a hydroxyl group. 5. Kationski polimer na bazi glikogena prema zahtjevu 4, naznačen time, da je R1 atom vodika ili karboksimetil-skupina.5. Glycogen-based cationic polymer according to claim 4, characterized in that R1 is a hydrogen atom or a carboxymethyl group. 6. Kationski polimer na bazi glikogena prema bilo kojem od prethodnih zahtjeva, naznačen time, da su X1 i X2 koji mogu biti isti ili različiti, skupina koja sadrži dušik –NHR2, u kojoj R2 je atom vodika ili H-[NH-(C1-C4)alkil]p-, gdje p je cijeli broj veći od ili jednak 1, a (C1-C4)alkil-skupine mogu biti iste ili različite.6. Glycogen-based cationic polymer according to any of the preceding claims, characterized in that X1 and X2, which may be the same or different, are a nitrogen-containing group –NHR2, in which R2 is a hydrogen atom or H-[NH-(C1 -C4)alkyl]p-, where p is an integer greater than or equal to 1, and the (C1-C4)alkyl groups can be the same or different. 7. Kationski polimer na bazi glikogena prema zahtjevu 6, naznačen time, da navedena skupina H-[NH-(C1-C4)alkil]p- je polietilenimin, s molekularnom masom od 50 do 3000 daltona, spermin (H2N(CH2)3NH(CH2)4NH(CH2)3NH2), ili spermidin (H2N(CH2)4NH(CH2)4NH2).7. Glycogen-based cationic polymer according to claim 6, characterized in that the specified group H-[NH-(C1-C4)alkyl]p- is polyethyleneimine, with a molecular weight of 50 to 3000 daltons, spermine (H2N(CH2)3NH (CH2)4NH(CH2)3NH2), or spermidine (H2N(CH2)4NH(CH2)4NH2). 8. Kationski polimer na bazi glikogena prema bilo kojem od prethodnih zahtjeva, naznačen time, da navedene ponavljajuće jedinice (a) i (b) obuhvaćaju sljedeće: - najmanje jednu skupinu koja sadrži dušik, koja se može ionizirati na fiziološkoj pH-vrijednosti, odabranu iz skupine koja se sastoji od sljedećih: NH2-(C1-C6)alkil, [N,N-di(C1-C6)alkilamino]-(C1-C6)alkil, NH2-(C1-C6)alkilamino}- (C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkilamino}-(C1-C6)alkil i azociklil-(C1-C6)alkil; i - najmanje jednu skupinu koja sadrži dušik, koja se može ionizirati na pH-vrijednosti nižoj od fiziološke pH, odabranu iz skupine koja se sastoji od sljedećih: NH2-{[(C1-C3)alkil]-di(C1-C6)alkilamonij}-(C1-C6)alkil i{[N,N-di(C1-C3)alkil-amino]-(C1-C6)alkil-di(C1-C6)alkilamonij}-(C1-C6)alkil. 8. Glycogen-based cationic polymer according to any of the preceding claims, characterized in that said repeating units (a) and (b) comprise the following: - at least one group containing nitrogen, which can be ionized at physiological pH-value, selected from the group consisting of the following: NH2-(C1-C6)alkyl, [N,N-di(C1-C6)alkylamino]- (C1-C6)alkyl, NH2-(C1-C6)alkylamino}- (C1-C6)alkyl, {[N,N-di(C1-C6)alkylamino]-(C1-C6)alkylamino}-(C1- C6)alkyl and azocyclyl-(C1-C6)alkyl; and - at least one group containing nitrogen, which can be ionized at a pH-value lower than the physiological pH, selected from the group consisting of the following: NH2-{[(C1-C3)alkyl]-di(C1-C6)alkylammonium} -(C1-C6)alkyl and {[N,N-di(C1-C3)alkyl-amino]-(C1-C6)alkyl-di(C1-C6)alkylammonium}(C1-C6)alkyl. 9. Kompleks između kationskog polimera na bazi glikogena prema bilo kojem od zahtjeva 1 do 8 i jednog anionskog spoja, naznačen time, da je navedeni anionski spoj odabran iz skupine koja se sastoji od jedne djelatne tvari i jedne nukleinske kiseline.9. A complex between a cationic glycogen-based polymer according to any one of claims 1 to 8 and an anionic compound, characterized in that said anionic compound is selected from the group consisting of one active substance and one nucleic acid. 10. Kompleks prema zahtjevu 9, naznačen time, da navedeni kompleks obuhvaća količinu spomenutog anionskog spoja koja iznosi između 5% i 60% po masi u odnosu na masu navedenog kationskog polimera na bazi glikogena. 10. Complex according to claim 9, characterized in that said complex comprises the amount of said anionic compound which is between 5% and 60% by mass in relation to the mass of said cationic glycogen-based polymer. 11. Kompleks prema zahtjevu 10, naznačen time, da navedeni kompleks obuhvaća količinu spomenutog anionskog spoja koja iznosi između 10% i 50% po masi u odnosu na masu navedenog kationskog polimera na bazi glikogena.11. The complex according to claim 10, characterized in that said complex comprises an amount of said anionic compound which is between 10% and 50% by mass in relation to the mass of said cationic glycogen-based polymer. 12. Farmaceutski sastav, naznačen time, da obuhvaća (A) kompleks između (1) kationskog polimera na bazi glikogena koji obuhvaća najmanje jednu ponavljajuću jedinicu odabranu iz skupine koja se sastoji od sljedećih: (a) u kojoj su skupine R koje mogu biti iste ili različite, atom vodika, karboksimetil-skupina, opcionalno u obliku soli s farmaceutski prihvatljivom organskom ili anorganskom bazom, ili skupina koja sadrži dušik odabrana od sljedećih: NH2-(C1-C6)alkil, [N,N-di(C1-C6)alkilamino]-(C1-C6)alkil, NH2-{[(C1-C6)alkil-di(C1-C6)alkilamonij]}-(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkil-di(C1-C6)alkilamonij}-(C1-C6)alkil, NH2-[(C1-C6)alkilamino]-(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkilamino}-(C1-C6)alkil, [tri(C1-C6)alkilamonij]-(C1-C6)alkil, azociklil-(C1-C6)alkil, gdje su (C1-C6)alkil-lanci koji mogu biti isti ili različiti, opcionalno supstituirani s jednom ili više hidroksil-skupina, i n je cijeli broj veći od ili jednak 1; i (b) u kojoj R1 je odabran od atoma vodika, karboksimetil-skupine, opcionalno u obliku soli s farmaceutski prihvatljivom organskom ili anorganskom bazom, ili skupina koja sadrži dušik odabrana od sljedećih: NH2-(C1-C6)alkil, [N,N-di(C1-C6)alkilamino]-(C1-C6)alkil, NH2-[(C1-C6)alkil-di(C1-C6)alkilamonij] -(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkil-di(C1-C6)alkilamonij}-(C1-C6)alkil, NH2-[(C1-C6)alkilamino]-(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkilamino}-(C1-C6)alkil, [tri(C1-C6)alkilamonij]-(C1-C6)alkil,gdje su (C1-C6)alkil-lanci koji mogu biti isti ili različiti, opcionalno supstituirani s jednom ili više hidroksil-skupina; se kod X1 i X2 koji mogu biti isti ili različiti, radi o skupini –OH ili skupini koja sadrži dušik –NHR2, u kojoj je R2 odabran od sljedećih: atom vodika, (C1-C6)alkil, H-[NH-(C1-C6)alkil]p-, dok p je cijeli broj veći od ili jednak 1, a (C1-C6)alkil-skupine mogu biti iste ili različite; i m je cijeli broj veći od ili jednak 1; uz uvjet da je najmanje jedan između R, R1, X1 i X2, takva skupina koja sadrži dušik kao što je definirano, odgovarajuće za svaki od R, R1, X1 i X2, i (2) anionskog spoja, pri čemu je spomenuti anionski spoj odabran iz skupine koja se sastoji od jedne djelatne tvari i jedne nukleinske kiseline; te (B) najmanje jedno farmaceutski prihvatljivo pomoćno sredstvo.12. A pharmaceutical composition characterized in that it comprises (A) a complex between (1) a cationic glycogen-based polymer comprising at least one repeating unit selected from the group consisting of the following: (And) where are R groups which may be the same or different, a hydrogen atom, a carboxymethyl group, optionally in the form of a salt with a pharmaceutically acceptable organic or inorganic base, or a nitrogen-containing group selected from the following: NH2-(C1-C6)alkyl, [N, N-di(C1-C6)alkylamino]-(C1-C6)alkyl, NH2-{[(C1-C6)alkyl-di(C1-C6)alkylammonium]}-(C1-C6)alkyl, {[N, N-di(C1-C6)alkylamino]-(C1-C6)alkyl-di(C1-C6)alkylammonium}-(C1-C6)alkyl, NH2-[(C1-C6)alkylamino]-(C1-C6) alkyl, {[N,N-di(C1-C6)alkylamino]-(C1-C6)alkylamino}(C1-C6)alkyl, [tri(C1-C6)alkylammonium]-(C1-C6)alkyl, azocyclyl -(C1-C6)alkyl, where the (C1-C6)alkyl chains, which may be the same or different, are optionally substituted with one or more hydroxyl groups, and n is an integer greater than or equal to 1; and (b) where R1 is selected from a hydrogen atom, a carboxymethyl group, optionally in the form of a salt with a pharmaceutically acceptable organic or inorganic base, or a nitrogen-containing group selected from the following: NH2-(C1-C6)alkyl, [N,N-di(C1- C6)alkylamino]-(C1-C6)alkyl, NH2-[(C1-C6)alkyl-di(C1-C6)alkylammonium] -(C1-C6)alkyl, {[N,N-di(C1-C6) alkylamino]-(C1-C6)alkyl-di(C1-C6)alkylammonium}-(C1-C6)alkyl, NH2-[(C1-C6)alkylamino]-(C1-C6)alkyl, {[N,N- di(C1-C6)alkylamino]-(C1-C6)alkylamino}-(C1-C6)alkyl, [tri(C1-C6)alkylammonium]-(C1-C6)alkyl, where (C1-C6)alkyl- chains which may be the same or different, optionally substituted with one or more hydroxyl groups; where X1 and X2, which may be the same or different, are the group –OH or the group containing nitrogen –NHR2, in which R2 is selected from the following: hydrogen atom, (C1-C6)alkyl, H-[NH-(C1 -C6)alkyl]p-, while p is an integer greater than or equal to 1, and the (C1-C6)alkyl groups can be the same or different; and m is an integer greater than or equal to 1; provided that at least one of R, R1, X1 and X2 is such a nitrogen-containing group as defined corresponding to each of R, R1, X1 and X2, and (2) an anionic compound, wherein said anionic compound is selected from the group consisting of one active substance and one nucleic acid; and (B) at least one pharmaceutically acceptable excipient. 13. Farmaceutski sastav prema zahtjevu 12, naznačen time, da spomenuti anionski spoj je jedna nukleinska kiselina.13. Pharmaceutical composition according to claim 12, characterized in that said anionic compound is a nucleic acid. 14. Farmaceutski sastav prema prethodnim zahtjevima 12 ili 13, naznačen time, da se upotrebljava za injektibilnu primjenu.14. Pharmaceutical composition according to previous claims 12 or 13, characterized in that it is used for injectable administration. 15. Kompleks, naznačen time, da je između (1) kationskog polimera na bazi glikogena koji obuhvaća najmanje jednu ponavljajuću jedinicu odabranu iz skupine koja se sastoji od sljedećih: (a) u kojoj su skupine R koje mogu biti iste ili različite, atom vodika, karboksimetil-skupina, opcionalno u obliku soli s farmaceutski prihvatljivom organskom ili anorganskom bazom, ili skupina koja sadrži dušik odabrana od sljedećih: NH2-(C1-C6)alkil, [N,N-di(C1-C6)alkilamino]-(C1-C6)alkil, NH2-{[(C1-C6)alkil-di(C1-C6)alkilamonij]}-(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkil-di(C1-C6)alkilamonij}-(C1-C6)alkil, NH2-[(C1-C6)alkilamino]-(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkilamino}-(C1-C6)alkil, [tri(C1-C6)alkilamonij]-(C1-C6)alkil, azociklil-(C1-C6)alkil, gdje su (C1-C6)alkil-lanci koji mogu biti isti ili različiti, opcionalno supstituirani s jednom ili više hidroksil-skupina, i n je cijeli broj veći od ili jednak 1; i (b) kojoj R1 je odabran od atoma vodika, karboksimetil-skupine, opcionalno u obliku soli s farmaceutski prihvatljivom organskom ili anorganskom bazom, ili od skupine koja sadrži dušik odabrane od sljedećih: NH2-(C1-C6)alkil, [N,N-di(C1-C6)alkilamino]-(C1-C6)alkil, NH2-[(C1-C6)alkil-di(C1-C6)alkilamonij] -(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkil-di(C1-C6)alkilamonij}-(C1-C6)alkil, NH2-[(C1-C6)alkilamino]-(C1-C6)alkil, {[N,N-di(C1-C6)alkilamino]-(C1-C6)alkilamino}-(C1-C6)alkil, [tri(C1-C6)alkilamonij]-(C1-C6)alkil, gdje su (C1-C6)alkil-lanci koji mogu biti isti ili različiti, opcionalno supstituirani s jednom ili više hidroksil-skupina; se kod X1 i X2 koji mogu biti isti ili različiti, radi o skupini –OH ili skupini koja sadrži dušik –NHR2, u kojoj je R2 odabran od sljedećih: atom vodika, (C1-C6)alkil, H-[NH-(C1-C6)alkil]p-, dok p je cijeli broj veći od ili jednak 1, a (C1-C6)alkil-skupine mogu biti iste ili različite; i m je cijeli broj veći od ili jednak 1; uz uvjet da je najmanje jedan između R, R1, X1 i X2, takva skupina koja sadrži dušik kao što je definirano, odgovarajuće za svaki od R, R1, X1 i X2, i (2) anionskog spoja, pri čemu je spomenuti anionski spoj odabran iz skupine koja se sastoji od jedne djelatne tvari i jedne nukleinske kiseline, te time, da se kompleks upotrebljava kao sredstvo za isporuku ili transfekciju spomenutog anionskog spoja.15. A complex characterized in that it is between (1) a cationic glycogen-based polymer comprising at least one repeating unit selected from the group consisting of the following: (And) where are R groups which may be the same or different, a hydrogen atom, a carboxymethyl group, optionally in the form of a salt with a pharmaceutically acceptable organic or inorganic base, or a nitrogen-containing group selected from the following: NH2-(C1-C6)alkyl, [N, N-di(C1-C6)alkylamino]-(C1-C6)alkyl, NH2-{[(C1-C6)alkyl-di(C1-C6)alkylammonium]}-(C1-C6)alkyl, {[N, N-di(C1-C6)alkylamino]-(C1-C6)alkyl-di(C1-C6)alkylammonium}-(C1-C6)alkyl, NH2-[(C1-C6)alkylamino]-(C1-C6) alkyl, {[N,N-di(C1-C6)alkylamino]-(C1-C6)alkylamino}(C1-C6)alkyl, [tri(C1-C6)alkylammonium]-(C1-C6)alkyl, azocyclyl -(C1-C6)alkyl, where the (C1-C6)alkyl chains, which may be the same or different, are optionally substituted with one or more hydroxyl groups, and n is an integer greater than or equal to 1; and (b) which R1 is selected from a hydrogen atom, a carboxymethyl group, optionally in the form of a salt with a pharmaceutically acceptable organic or inorganic base, or from a nitrogen-containing group selected from the following: NH2-(C1-C6)alkyl, [N,N-di(C1 -C6)alkylamino]-(C1-C6)alkyl, NH2-[(C1-C6)alkyl-di(C1-C6)alkylammonium] -(C1-C6)alkyl, {[N,N-di(C1-C6 )alkylamino]-(C1-C6)alkyl-di(C1-C6)alkylammonium}-(C1-C6)alkyl, NH2-[(C1-C6)alkylamino]-(C1-C6)alkyl, {[N,N-di(C1-C6)alkylamino]-(C1-C6)alkylamino}-(C1-C6)alkyl, [tri(C1-C6)alkylammonium]-(C1-C6)alkyl, where ( C1-C6) alkyl chains which may be the same or different, optionally substituted with one or more hydroxyl groups; where X1 and X2, which may be the same or different, are the group –OH or the group containing nitrogen –NHR2, in which R2 is selected from the following: hydrogen atom, (C1-C6)alkyl, H-[NH-(C1 -C6)alkyl]p-, while p is an integer greater than or equal to 1, and the (C1-C6)alkyl groups can be the same or different; and m is an integer greater than or equal to 1; provided that at least one of R, R1, X1 and X2 is such a nitrogen-containing group as defined corresponding to each of R, R1, X1 and X2, and (2) an anionic compound, wherein said anionic compound is selected from the group consisting of one active substance and one nucleic acid, and thereby, that the complex is used as a means of delivery or transfection of the mentioned anionic compound.
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